Facile Photochemical Synthesis of 1,1′-Binaphthyls

Pablo Wessig; Gunnar Müller

doi:10.1071/CH08141

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Facile Photochemical Synthesis of 1,1′-Binaphthyls

Pablo Wessig ^A ^B and Gunnar Müller ^A

+ Author Affiliations

- Author Affiliations

^A Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Strasse 2, D-12489 Berlin, Germany.

^B Corresponding author. Email: pablo.wessig@chemie.hu-berlin.de

Australian Journal of Chemistry 61(8) 569-572 https://doi.org/10.1071/CH08141
Submitted: 5 April 2008 Accepted: 18 June 2008 Published: 15 August 2008

Abstract

The photochemical synthesis of highly functionalized 1,1′-binaphthyls 9 by photodehydro-Diels–Alder reaction of esters 8 is reported. It was found that π-stacking interactions between a naphthyl moiety already present in the reactants 8 and an aryl group tethered in the propargyl position of these esters clearly influence the regio- and diastereoselectivity of the reaction. The formation of undesired phenanthrenes 10 could be suppressed by introduction of a blocking methoxy group in the 2-position of the naphthyl moiety. In one case, a diastereomeric ratio of 32:68 was achieved. This is the first example of an atropselective synthesis of biaryls by a photodehydro-Diels–Alder reaction.

References

Facile Photochemical Synthesis of 1,1′-Binaphthyls

Abstract

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